mental chess

I meant my reply as my own interpretation of life and my personal existential crises that I went through, not to challenge your ideas. Hopefully it didn't come across as confrontational or as a cristism.

I shifted careers from fire protection to becoming a social worker (counselor/therapist) because I always found psychology really fascinating and enjoy that type of work. So I sold my house and went back to university for 5 years to get a BA in psychology and a Masters in social work. It took several years to make the decision and I went back and forth for a really long time (2-3 years maybe) because of a lot of things you mentioned in your post regarding your friend - changing careers meant giving up a stable job, house, savings and everything I worked for...etc. but it meant that I was pursuing something new that I enjoy. In the end it had to be done because I was depressed with life doing a meaningless career to me. I really didn't care if I was alive or dead at that point so i had to make the change. Life felt pointless to me to spend all my time doing something that was boring that I didn't enjoy.

I find that the biggest pressure is the one we put on ourselves.

Yes definitely. I agree. We create our own barriers.

sit in nature, maybe reading or painting.

Sounds like an enjoyable life for sure.

If you would ask yourself this question now, what would be the answer?

I think that question is best used for someone experiencing a dilemma or dissonance in life, like your friend. Someone who has everything that they thought they wanted in their life, that they learned are the things that bring happiness (money, good job, possessions...etc), yet are unhappy with their current situation and don't know what they want to do or how to change. It's meant as a "power" question to elicit change and overcome mental barriers. It's like, the person thought they wanted "X" and that it would bring them happiness. They obtained "X" and yet they are unhappy. The choice then is to keep doing "X" and live their entire life being unhappy or they could pursue "Y" which they are passionate about and which gives them joy. "Y" is a risk of course and may mean that they have to give up all the benefits associated with "X," but they will be happy.

So for me if I asked myself that question 8 years ago I would have said go back to school and become a therapist.